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Product name: Kaempferol-3-Rutinoside
Synonym name: Nicotiflorin; Nicotifloroside
Catalogue No.: BP0823
Cas No.: 17650-84-9
Formula: C27H30O15
Mol Weight: 594.522
Botanical Source: numerous plant spp. for example Sophora japonica, Chromolaena moritziana , Mitracarpus scaber
Physical Description: Yellow powder
Type of Compound: Flavonoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.
Descriptions:
Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Flos Carthami, it has a protective effect against cerebral ischemic damage.[1]
Nicotiflorin has protective effects on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.[2]
Nicotiflorin has neuro-protection in permanent focal cerebral ischemia and in neuronal cultures. [3]
References:
[1] Li R, Guo M, Zhang G, et al. J Ethnopharmacol, 2006, 107(1):143-50.
[2] Huang J, Fu S Y, Cao Y, et al. Pharmacol Biochem Behavior, 2007, 86(4):741-8.
[3] Li R, Guo M, Zhang G, et al. Biol Pharm Bull, 2006, 29(9):1868-72.
[4] Sun J, Xiao-Juan H E, Liu J Q. China Pharmacy, 2015, 9.
HPLC of Kaempferol-3-Rutinoside
HNMR of Kaempferol-3-Rutinoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
249.2000
-.2757
-.3787
2.4253
.3942
.1710
Low
77.3657
4.6805
Yes
No
Yes
No
Yes
No
0.6
Yes
Yes
Yes
Yes
Kaempferol-3-O-rutinoside (CAS No. 17650-84-9), as a natural flavonoid compound, has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique structural characteristics and diverse biological activities. This compound belongs to the Kaempferol O-glucoside class and is a disaccharide derivative formed by linking kaempferol to a rutin glycoside group at 3 position ([6-deoxy-α-L-mannose-(1→6)-β-D-glucosylate]). Kaempol-3-O-rutin was first isolated and identified from the leaves of Solanum campaniforme, a Solanaceae plant, and was later reported in various plants. As a natural flavonoid glycoside, it exhibits significant antioxidant, anti-inflammatory, and antitumor pharmacological activities, especially showing potential therapeutic value in regulating oxidative stress-related diseases.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of kaempol-3-O-rutin, druggability evaluation and pharmacokinetic characteristics, and, combined with current research progress, explore its clinical application prospects and future directions, providing theoretical basis and research reference for drug development of this natural product.
The molecular formula of kaempol-3-O-rutin is C27H30O15, with a molecular weight of 594.5220. Its core structure is a kaempferol flavonoid backbone, with three hydroxyl groups connected to the rutin sugar group via glycosidic bonds. The rutin sugar group consists of a 6-deoxy-α-L-mannose and a β-D-glucose bond connected by a 1→6 glycosidic bond, giving the molecule high polarity and water solubility.
In terms of physicochemical properties, the LogP value of kaempol-3-O-rutin is about -0.2757, indicating strong hydrophilicity, with a water solubility test value of 2.4253, supporting its good water solubility. The topological pole surface area (TPSA) reaches as high as 249.2 Ų, reflecting the presence of many polar groups on the molecular surface, which facilitates hydrogen bonding and electrostatic interactions with biological macromolecules. This compound has low blood-brain barrier permeability, suggesting limited penetration in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk and meeting safety requirements.
Structurally, kaempol-3-O-rutin belongs to the rutin class and exhibits the typical structural features of trihydroxyflavones. The disaccharide portion not only improves its water solubility but may also affect its bioavailability and metabolic stability.
Kaempol-3-O-rutin was originally isolated from Solanum campaniforme leaves. Additionally, this compound has been reported in various plants, especially in vegetables, fruits, and medicinal plants rich in flavonoid glycosides. Common plant sources include Solanaceae, Brassicaceae, and legumes, where the content of snarophenol-3-O-rutin varies depending on species, ecological environment, and growth stage.
The extraction method mainly uses polar solvents, such as ethanol, water, or their mixed solvent systems, improving extraction efficiency through modern technologies like reflux extraction, ultrasound-assisted extraction, or microwave-assisted extraction. The extract undergoes concentration, liquid-liquid distribution, and multi-stage column chromatography purification, followed by component identification and purity confirmation using high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR).
In recent years, green and efficient extraction technologies such as supercritical fluid extraction and membrane separation have gradually been applied to the extraction of these flavonoid glycosides, significantly improving extraction purity and yield, and reducing solvent consumption and environmental pollution.
Kaempol-3-O-rutin, as a typical trihydroxyflavonoid glycoside, exhibits strong antioxidant capacity. In vitro studies have shown that this compound can effectively scavenge various free radicals, including hydroxyl radicals (· OH), superoxide anion (O2·-), and hydrogen peroxide (H2O2) significantly inhibit lipid peroxidation and DNA oxidative damage. Its antioxidant mechanism is mainly achieved through direct electron donor action and metal ion chelation.
Multiple cell model studies have confirmed that kaemprol-3-O-rutin can significantly reduce cell damage caused by oxidative stress. In human hepatocyte, nerve cell, and cardiomyocyte models, this compound enhances cellular tolerance to oxidative damage by activating intracellular antioxidant enzyme systems, thereby promoting cell survival.
Flavonoid compounds generally have anti-inflammatory activity, and kaempol-3-O-rutin glycosides are no exception. It can inhibit the expression of inflammatory mediators such as TNF-α, IL-6, and IL-1β, reducing inflammatory responses. Related studies have shown that this compound exerts immunomodulatory effects by modulating the NF-κB signaling pathway, reducing the activity of pro-inflammatory enzymes.
Preliminary in vitro experiments have revealed that kaemprol-3-O-rutin has inhibitory effects on proliferation and apoptosis induction in various tumor cells. Its mechanism involves cell cycle arrest, mitochondrial pathway-mediated apoptosis, and oxidative stress regulation, suggesting its potential as a natural antitumor drug.
In addition, kaemprol-3-O-rutin also shows certain activity in antibacterial, antiviral, neuroprotection, and cardiovascular protection, with related research continuing to deepen.
The pharmacological core of kaempol-3-O-rutin lies in its regulation of oxidative stress-related signaling pathways, especially by activating the nuclear factor red blood cell 2-associated factor 2 (NFE2L2/NRF2) pathway to achieve cellular protection. NRF2, as a key intracellular antioxidant transcription factor, regulates the expression of various antioxidant enzyme genes, including superoxide dismutase (SOD1, SOD2), catalase peroxide (CAT), glutathione peroxidase (GPX1), and heme oxygenase-1 (HMOX1).
Kaempol-3-O-rutin promotes NRF2 nuclear translocation, enhances its binding to antioxidant reaction elements (ARE), induces expression of downstream antioxidant enzyme genes, enhances cellular antioxidant defense, reduces ROS accumulation, and alleviates oxidative damage. Additionally, this compound can inhibit pro-inflammatory signaling pathways such as NF-κB, reducing the release of inflammatory mediators and alleviating inflammatory responses.
In apoptosis regulation, kaempol-3-O-rutin promotes the activation of apoptosis-related enzymes by modulating Bcl-2 family proteins and mitochondrial membrane potentials, thereby inducing programmed tumor cell death. Its impact on the cell cycle manifests as G1/S phase blockade, inhibiting cell proliferation.
In summary, the multi-target mechanism of kaempol-3-O-rutin provides a molecular basis for its broad pharmacological activity, especially showing significant therapeutic potential in diseases related to antioxidant damage.
The druggability evaluation of kaempol-3-O-rutin showed good safety and suitable pharmacokinetic characteristics. Its molecular weight is 594.5, slightly above the ideal range for traditional small molecule drugs, but its high polarity and water solubility help improve its distribution in the body. A negative LogP value indicates strong hydrophilicity, which may limit its passive diffusion through lipid membranes but facilitates dissolution and transport in plasma.
The low permeability of the blood-brain barrier suggests its potential limitations in central nervous system diseases, but it also reduces the risk of potential CNS toxicity. The hERG channel inhibition test was negative, indicating good cardiac safety. Ames test results showed no significant genotoxicity, supporting its safety for long-term use.
In terms of pharmacokinetics, current research is relatively limited. Preliminary in vivo studies show that physanol-3-O-rutin is absorbed slowly after oral administration, with limited bioavailability, possibly due to its large molecular weight and glycoside structure. In the body, it is mainly hydrolyzed by the gut microbiota into kaempferol, which is an active metabolite and exerts pharmacological effects. Metabolic pathways include phase I and phase II metabolic reactions in the liver, mainly excreted through glucuronylation and sulfation.
In the future, further systematic research on pharmacokinetics and pharmacodynamics is needed to optimize delivery routes and dosage form design to improve bioavailability and clinical application potential.
Based on the significant antioxidant and cell-protective activities of kaempol-3-O-rutin, its clinical application prospects in various oxidative stress-related diseases are broad. Oxidative stress is an important pathogenic mechanism of cardiovascular diseases, neurodegenerative diseases, diabetes, and tumors. Kaempol-3-O-rutin activates the NRF2 signaling pathway, enhancing endogenous antioxidant defenses and offering potential preventive and therapeutic value.
In cardiovascular diseases, this compound can alleviate ischemia-reperfusion injury, inhibit the progression of atherosclerosis, and protect myocardial cell function; In neurological diseases, although the blood-brain barrier has low permeability, its metabolite kaempferol may have neuroprotective effects and has potential adjunctive therapeutic value for Alzheimer's disease, Parkinson's disease, and others.
In addition, the anti-inflammatory and antitumor activities of kaempol-3-O-rutin offer new ideas for the treatment of inflammatory diseases and tumors. Combining modern drug delivery systems, such as nanocarriers and targeted drug delivery technologies, is expected to overcome their insufficient bioavailability and improve clinical efficacy.
Future research should focus on:
Kaempol-3-O-rutin, as an important natural flavonoid glycoside, demonstrates broad pharmacological effects and good safety due to its unique chemical structure and significant antioxidant, anti-inflammatory, and antitumor activities. By regulating NRF2 and related antioxidant enzyme targets, it exerts cellular protection and disease intervention effects, providing a new natural drug candidate molecule for the treatment of oxidative stress-related diseases.
Although research on its pharmacokinetics and clinical applications is still in its early stages, with advances in extraction and purification technologies and drug delivery systems, kaempol-3-O-rutin is expected to become an important direction for natural product drug development. In the future, it is necessary to strengthen interdisciplinary research to move from the laboratory to clinical practice, ultimately achieving its widespread application in disease prevention and treatment.
Shenshuai
Wenjing
Hedandan
